5 Improv Comedy Skills that Made Me a Better CEO

Not everyone knows this, but for the past few years I’ve been living a double-life. After long days as CEO of RJMetrics, I’ve made a habit of sneaking off to musty classrooms and tiny theaters to learn and perform improv comedy. This spring, I was honored to join Big Baby, a resident “house team” at Philly Improv Theater.

As it turns out, I’m not the only one. A far more seasoned CEO, Twitter’s Dick Costolo, has a background in comedy as well. While listening to his awesome University of Michigan commencement speech recently, I couldn’t help but reflect on the fact that doing improv and running a business actually have a lot in common.

While both pursuits are fun and accessible for beginners, they also contain deep layers of nuance that separate the good from the great. As I’ve worked to peel back these layers, more and more of my improv skills have started showing up in my day job. These are my favorites.

1. “Yes, and…”

On the first day of Improv 101, they teach you to say “yes, and…” to everything your scene partner says. In other words, agree with the reality they are creating and then contribute new information that adds to that reality.

On the surface, this would be terrible advice for a CEO. One of the most important parts of my job is saying “no.” With limited bandwidth, startups can only pursue a minuscule fraction of ideas available and must kick the rest to the curb.

Buried under the “yes, and…” idea, however, is a deeper lesson about listening to your scene partner and exploring your shared reality together. In a startup, your teammates are there because you’ve chosen them—hopefully you have some faith in their ideas. Even when you disagree with an idea at the outset, it’s important that you don’t make the conversation a two-line scene that ends in “no.”

Exploring new ideas with a “yes, and…” conversation forces a deeper level of scrutiny, leading to questions like “if this is true, what else is true?” This will inevitably lead to a discussion about the “why” that originated this idea in the first place.

Navigating these conversations will require you to maintain a well-thought-out and defensible vision for where your company is headed. While most ideas will still end up on the curb, the idea owner will walk away empowered by a clearer understanding of this vision instead of frustration from outright rejection. And, if your experience is like mine, sometimes you’ll leave feeling like your own view of reality got a bit smarter, too.

2. State the Obvious

In an improv scene, 100% of the context is created on the spot. You have no background, no props, and no established relationships. If you don’t communicate an idea clearly, neither the audience nor your fellow performers can be expected to get it.

Improv has given me a lot of practice unambiguously communicating what’s important, even when it means sounding obtuse or stating things that seem obvious.

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I use these skills constantly as a CEO. Internally and externally, I repeat our most important ideas multiple times a day, every day. I try to frame every conversation, no matter how tactical, around these ideas. Sometimes I feel like a broken record, but when the audience is constantly changing, it’s the only way to ensure we’re all moving in the right direction.

3. Play the Long Game

A typical longform improv show is 22 minutes long, about the same length as a full sitcom (sans commercials). To fill that time in an entertaining way, complex characters need to develop and ideas need room to breathe. This means making thoughtful investments early on, like not saying that hilariously dismissive punchline that would stifle a scene or a character.

These investments can provide a huge payoff in the end, but require self-restraint and the ability to keep the long-term vision in mind. The best improv teams accomplish both: keeping the audience entertained with each step forward, while continuously building toward a strong finish.

Similarly, building a startup is about balancing quick wins against long-term vision. In our early days, we made the common mistake of taking on a customer that wasn’t a good fit because we wanted to make our sales numbers look as good as possible. Ultimately, as you might expect, the revenue was only temporary and the custom work it required distracted us from our core focus.

Today, we only go after “quick wins” when they also move us closer to our long-term goals. The balance of our time is focused on the long game. Maintaining this balance allows us to build strong momentum and know we’re being true to our vision.

4. The Team is the Star

At my improv shows, the crowd never hears my name. We’re announced as a team and our performance, good or bad, is a product of the group and not individual performers. If I’m having a bad night, I trust my team to support me in ways that make it unnoticeable. Similarly, the best improvisers shine by elevating the group’s performance before focusing on their own.

As a startup grows, this dynamic is something worth studying.

There is a rather morbid term in the business world known as the “bus factor.” For any given project or area of the business, the bus factor is the number of people who could get hit by a bus before no one is left who understands it. A well-managed company should have no key projects with a bus factor of 1 (and 2 should make you pretty uneasy).

An improv team’s bus factor is equal to the number of members on the team. Members can be slotted in and out of scenes and have total faith in each other to contribute where their counterparts have left off.

This doesn’t mean you shouldn’t hire “rock stars” or be one yourself. It means that the most valuable thing a rock star can do is leverage their skills to build a more cohesive, well-rounded team.

5. Blow Their Minds

To many, the mother of all longform improv show structures is The Harold. Through a series of group games and scenes, the Harold transforms a simple audience suggestion into a set of overarching themes and explores them through seemingly independent scenes that are eventually revealed to coexist in a shared universe. As you can imagine, this is extremely hard to do, let alone do well.

As our director likes to say, however, when The Harold is done right it will blow the audience’s minds.

When I think about public speaking, I think about The Harold. The structure is brilliant: you have a topic that could be mundane, but you look for the deep themes that make the topic worth exploring. You start with anecdotes or examples that stand alone as entertaining and self-contained case studies. Meanwhile, behind the scenes, you’re contemplating a bigger idea—a common thread that intertwines the anecdotes. Just when the audience thinks it’s over, you call out the big theme to drive home your core message. Minds blown.

Whether I’m speaking internally or externally, I try to present using some variation of this structure. It’s a helpful cheat-sheet for talking about vision without drowning in platitudes. And unlike with improv, you have the added benefit of being able to plan it ahead of time.

Conclusion

I used to tell people that I did improv because it exercised parts of my brain that I didn’t get to use as an entrepreneur. In retrospect, I think that claim does a disservice to both—I actually like them because of what they share.

Improv and entrepreneurship are delicate mixtures of art and science that require harmony between the left and right sides of the brain to master. I still have a lot to learn about both, but I’m confident that the time I’m investing will be well spent.

I’ve had a lot of fun thinking about how effective social media management is a lot like improv- you don’t just want to be awfully nice to people (which can seem awkward, fake or forced), you want to have fun, back-and-forth interactions with them. And then I started to see how it can actually apply to a lot of things beyond that, like you’ve shown. Fun post!

PS: Minor stylistic suggestion, I’d turn down the bold a little!

Sirita Wright

I was googling tips for improv conservatory auditions, I have one on Saturday, and your piece came up. I’am glad I read it. Its given me improv information that I can now read-up as I prepare for my audition. Also, as a business owner its given me solid advice and new perspectives to think on as I run my businesses, acting being one of them.